(±) Anabasine is a muscle relaxant used for muscle relaxation during surgery.

Physicochemical Properties

Molecular Formula	C10H14N2
Molecular Weight	162.23156
Exact Mass	162.115
CAS #	13078-04-1
PubChem CID	2181
Appearance	Light yellow to orange liquid
Density	1.0±0.1 g/cm3
Boiling Point	271.0±0.0 °C at 760 mmHg
Melting Point	9ºC
Flash Point	93.3±0.0 °C
Vapour Pressure	0.0±0.5 mmHg at 25°C
Index of Refraction	1.524
LogP	0.85
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Heavy Atom Count	12
Complexity	136
Defined Atom Stereocenter Count	0
SMILES	N1CCCCC1C1C=NC=CC=1
InChi Key	MTXSIJUGVMTTMU-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2
Chemical Name	3-piperidin-2-ylpyridine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics	Absorption, Distribution and Excretion Anabasine is readily absorbed from the skin and from mucous membranes. Metabolism / Metabolites IN VITRO METABOLISM OF (-)-METHYLANABASINE BY RAT, RABBIT & GUINEA PIG GAVE (-)-ANABASINE WHICH WAS METABOLIZED TO 1'-N-HYDROXYANABASINE & ANABASINE 1'DELTA-NITRONE. METABOLIC PRODUCTS OF FORTIFIED LUNG MICROSOMAL FRACTIONS WERE SIMILAR. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.
Toxicity/Toxicokinetics	Toxicity Summary Anabasine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. Interactions ANABASINE ENHANCED SEDATIVE ACTION OF RESERPINE, APOMORPHINE, & 5-HYDROXYTRYPTOPHAN IN FROGS & INHIBITED SEROTONIN UPTAKE BY HUMAN THROMBOCYTES.
Additional Infomation	Anabasine is a pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3. It has a role as a plant metabolite, a teratogenic agent and a nicotinic acetylcholine receptor agonist. It is a piperidine alkaloid and a pyridine alkaloid. Anabasine has been reported in Anabasis aphylla, Nicotiana tabacum, and Nicotiana with data available. Anabasine is a nicotine analog that is an alkaloid found in tree tobacco (Nicotiana glauca) and is comprised of a pyridine substituted by a piperidin-2-yl group at position 3. Anabasine has been used as an industrial insecticide and, since it is present in trace amounts in tobacco smoke, its detection in urine can be used as an indicator of exposure to tobacco smoke. Anabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. Anabasine is an unstable yellow liquid which is succeptable to light, heat and moisture. It's decomposition products include Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases and carbon dioxide. Anabasine is a pyridine alkaloid found in the stem of the (Nicotiana glauca) plant, a close relative of (Nicotiana tabacum) the common tobacco plant. Anabasine is a metabolite of nicotine which can be used as an indicator of a person's exposure to tobbacco smoke. A piperidine botanical insecticide. A piperidine botanical insecticide. See also: Anabasine (annotation moved to). Mechanism of Action ...ANABASINE AFFECT/S/ THE GANGLION OF THE INSECT CENTRAL NERVOUS SYSTEM, FACILITATING TRANS-SYNAPTIC CONDUCTION AT LOW CONCENTRATIONS AND BLOCKING CONDUCTION AT HIGHER LEVELS. ANABASINE EXERTED NEUROMUSCULAR BLOCKING EFFECT ON ISOLATED RAT PHRENIC NERVE-DIAPHRAGM WHICH COULD BE PARTIALLY ANTAGONIZED BY NEOSTIGMINE. IT IS A DEPOLARIZING MUSCLE RELAXANT WITH SOME CHARACTERISTICS OF COMPETITIVE MUSCLE RELAXANTS. Therapeutic Uses EXPTL USE: ANABASINE (2 MG/KG/DAY, IP FOR 10 DAYS) INHIBITED THE INHIBITORY EFFECT OF CONCOMITANTLY ADMIN HYDROCORTISONE ON ADRENAL CORTEX-PITUITARY SYSTEM IN RATS. IT ALSO INHIBITED ASEPTIC INFLAMMATION (FORMALIN INJECTION UNDER THE PLANTAR APONEUROSIS OF THE FOOT) IN RATS; THIS ANTIINFLAMMATORY ACTIVITY APPEARS TO BE DUE TO ACTIVATION OF ADRENAL CORTEX-HYPOTHALAMUS-PITUITARY SYSTEM. IT MAY BE USEFUL TO ACTIVATE THE HORMONAL FUNCTION OF ADRENAL CORTEX-PITUITARY SYSTEM DURING GLUCOCORTICOID THERAPY IN PATIENTS WITH INFLAMMATION.

Solubility Data

Solubility (In Vitro)

DMSO : ~130 mg/mL (~801.33 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.17 mg/mL (13.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.17 mg/mL (13.38 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.17 mg/mL (13.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.1641 mL	30.8204 mL	61.6409 mL
	5 mM	1.2328 mL	6.1641 mL	12.3282 mL
	10 mM	0.6164 mL	3.0820 mL	6.1641 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.